Tetrahydrofuran → HCID 53627949, compound

HRID 227028Notes

Reaction equation

HRID 227028 reaction equation
CON(C)C([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=2)[CH:7]=1)=O.I[C:27]1[CH:36]=[CH:35][C:34]2[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=2[N:28]=1.C([Mg]Cl)(C)C.C1C[O:45][CH2:44]C1>>[Br:24][C:20]1[N:19]=[C:18]([CH2:17][N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15](=[O:16])[C:6]([C:44]([C:27]3[CH:36]=[CH:35][C:34]4[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=4[N:28]=3)=[O:45])=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 577545321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amideHCID 57754569HCID 57754569, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 53627949HCID 53627949, compound

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60 from 327 mg (0.81 mmol) of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 4 mL THF and 527 mg (2.03 mmol) of 2-iodo-5,6,7,8-tetrahydro-quinoline in 2 mL THF with 1.01 mL 2M isopropylmagnesium chloride. Yield: 28 mg of a white powder. LC-MSD, m/z for C25H20BrN3O2 [M+H]+=474.0, 476.0; HPLC retention time: 2.5 min.

Sources & evidence

ORD record
ord-1f092830a58f47929b36b3e1281ce539
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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